1-oxo-3-(2,4,6-trimethoxyphenyl)-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-oxo-3-(2,4,6-trimethoxyphenyl)-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester
• 英文别名: methyl (1S,2S)-3-oxo-1-(2,4,6-trimethoxyphenyl)-1,2,4,5,6,7-hexahydroindene-2-carboxylate
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: AXGRHZAFVDFBRT-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 哌啶 、 copper(II) bis(trifluoromethanesulfonate) 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 0.25h， 生成 1-oxo-3-(2,4,6-trimethoxyphenyl)-2,3,4,5,6,7-hexahydro-1H-indene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Polarizing the Nazarov Cyclization:  Efficient Catalysis under Mild Conditions

  摘要：

  Substituted divinyl ketones were studied in the Nazarov cyclization. alpha-Carbomethoxy divinyl ketones underwent efficient Nazarov cyclization with catalytic copper triflate (2 mol %) to give a single cyclopentenone regio- and stereoisomer. The efficiency of the cyclizations correlated with the ability of the substituents to favorably polarize the pi-system of the cationic intermediate.

  DOI：

  10.1021/ja037910b

文献信息

• Polarizing the Nazarov Cyclization:  The Impact of Dienone Substitution Pattern on Reactivity and Selectivity
  作者：Wei He、Ildiko R. Herrick、Tulay A. Atesin、Patrick A. Caruana、Colleen A. Kellenberger、Alison J. Frontier

  DOI：10.1021/ja077162g

  日期：2008.1.1

  The impact of dienone substitution on the Nazarov cyclization has been examined in detail. Substrates bearing different substituents at each of four positions on the dienone backbone were systematically probed in order to identify trends leading to higher reactivity and better selectivity. Desymmetrization of the pentadienyl cation and oxyallyl cation intermediates through placement of polarizing groups

  详细研究了二烯酮取代对 Nazarov 环化的影响。为了确定导致更高反应性和更好选择性的趋势，系统地探测了在二烯酮骨架的四个位置的每个位置上带有不同取代基的底物。发现通过在 C-2 和 C-4 位置放置极化基团使戊二烯基阳离子和氧烯丙基阳离子中间体去对称化特别有效。这些修饰允许在催化量的温和路易斯酸存在下发生环化。还发现亚烷基β-酮酯的E和Z异构体的混合物的立体会聚环化通过在反应条件下发生的有效异构化过程发生。
• Polarizing the Nazarov Cyclization:  Efficient Catalysis under Mild Conditions
  作者：Wei He、Xiufeng Sun、Alison J. Frontier

  DOI：10.1021/ja037910b

  日期：2003.11.1

  Substituted divinyl ketones were studied in the Nazarov cyclization. alpha-Carbomethoxy divinyl ketones underwent efficient Nazarov cyclization with catalytic copper triflate (2 mol %) to give a single cyclopentenone regio- and stereoisomer. The efficiency of the cyclizations correlated with the ability of the substituents to favorably polarize the pi-system of the cationic intermediate.